A Brand New Experience

by falcon29

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma, Consensual, Romantic, BiSexual, Shemale, Fiction, Anal Sex, First, .

Desc: Erotica Sex Story: A guy finds pleasure in a new way.

A friend of mine named Andy had gotten divorced in April. By the time our neighborhood had its July 4th barbecue, he had fallen into the deepest funk I’ve ever seen. He was coming in late to work, often in the same suit he’d worn the previous day. I’m not sure if he even wore a clean shirt or underwear. He called in sick a few times, too.

We were basically equal on our company ladder and every job I completed usually went to his department for the next step. We had lunch together almost every day and had been fishing buddies before the divorce, but I hadn’t been able to shake him loose to go out in my boat since just after his wife wiped him out. She got the best of their cars and a lion’s share of the money from the house sale, plus alimony.

My name’s Pete, by the way. I have a wife and, though we aren’t Romeo and Juliet (though her name IS Julie), we still get along mostly. No kids in the seven years we’ve been together. Andy didn’t have kids either, fortunately, or she’d have probably gotten all the money from the house.

The neighborhood barbecue is a lot of fun usually. There’s this one guy though who always arrives drunk and gets worse until he passes out or storms off, angry a somebody – usually his wife. But most of us get along, at least for that one day. We live on a cul-de-sac and the county has allowed us to close it off to outside traffic for the afternoon. We set the (safe and sane, of course) fireworks off once it gets dark enough.

Like I said, it’s a lot of fun. It isn’t restricted, in the sense that any of us may invite relatives or friends as long as they kick in for the pot luck. Burgers, hot dogs, buns, beer or booze, etc. even chips. Chips must be accompanied by one of the former to qualify.

That year I stopped by Andy’s desk the day before to drop off some paperwork he’d asked for. I asked him what he was doing for the long weekend.

“Aw, nothin’,” he said morosely. The corner of his mouth curved into a sarcastic half-smile. He kind of snorted before adding, “Maybe I’ll go get drunk for a change.”

“Well, come on over and get drunk with us. The ‘BBQ’ is tomorrow. Bring some buns and a six pack and drink free all afternoon!” We also had some really good weed, and Andy and I have smoked together before but it wasn’t the kind of office where you talk about that openly.

He hadn’t looked straight at me since I first came in but he raised his head up then. The old look the divorce had stolen from him came into his eyes. “That’s right. Your block party. I took ... her a couple years ago.” He looked out the window and said no more.

“So ... does that mean you want to come?”

“I do want to – at least right now. Let me see how I feel in the morning and I’ll give you a call.”

“Okay. Or, don’t bother calling unless you want to. Bring something you want to drink and share, and some hot dog or burger buns to share. If you don’t show up I’ll figure it out.” He looked back at me and said that sounded good. I started to leave, but I turned around. Trying to sound like a friend, not a parent or doctor, when I suggested, “Maybe, you know, you can ‘tap her light’, as we used to say, tonight. Maybe you’ll feel better tomorrow.” If he got wasted I knew he’d feel like shit the next day.

He looked at me for a second before he sighed, nodded and said, “Yeah, I know buddy. Maybe we can talk some tomorrow.” He knew he’d been fucking up.

“Sure. I’ll really try to make it, Pete.” I left, not knowing if he’d show up or not.

This is where the story really starts. The weather was fine on Saturday. There are six houses around the bulbous and distended dead end that is Winston Street. Julie and I live in one of the end houses. We have started to all chip in on the rent for a canopy for shade as well as in case of rain. It was set up by two of the neighbors before nine A.M. A half hour later I wheeled my barbecue grill out and lined it up next to the three others already there. One of them was a combined grill and smoker. The guy had started the fire before dawn and claimed he had a brisket and several racks of ribs in it already.

We had the tables set up and the coolers (and wheelbarrows) iced down. One of the guys had strung an extension cord out and wheeled out his apartment-sized garage refrigerator and plugged it in. Emptied of everything else, there was room for all the salads, meat, some ice cream, etc. That was a great thing to do. But when he suggested dragging out his flat screen so we could watch the game, it was voted down by most of us.

As I said, I have a boat. So I’m not one of the two of the homes on the street that had a pool in the back yard. But they were both open for use. A couple people had invited relatives. Added to the relatives and friends, we were too large a group to have the party in either of the ‘pool yards’, had we even wanted to, which I didn’t.

Grills were lit and all the guys had a beer in hand by noon. For more than one of them it was not the first of the day (Julie and I had smoked our pre-party joint in the house before coming outside). Kids started griping so we started cooking. Most of the adults were satisfied with their drinks and chips, and the usual snacks from the dishes spread out on the tables.

About two o’clock, Andy walked up the street carrying groceries. I waved him over toward the coolers and ‘fridge. “Glad you could make it, man, really!” He looked better than he had for a month at least. Under the canopy he took off his sunglasses and looked around. All the red eye effect of his recent debauchery had nearly disappeared. I slapped his back and helped him stash the food and drinks he brought before settling down with a beer.

“You know, Pete, this is nice. I wish we could have had friends like these when I was married. Maybe ... well, it might have made a difference.”

“Maybe,” I said. “But probably not. It always seemed to me you were different when I saw the two of you together. It was like ... I don’t know. Like you did everything to please her and she still wasn’t satisfied.” We moved into my house so we could burn a joint.

“Yeah. You’re right, Pete. Nothing I did ever seemed to be enough – in any way.”

“As devastating as it all was – the divorce and all the arguing – I think you’re better off without her.”

When the joint was gone we went back outside. The party had grown some with the people who had arrived while we were absent. Andy had met a few of my neighbors previously, and we mingled. As he became more comfortable (And stoned), Andy relaxed and began to circulate on his own.

The rest of this story I got from Andy. It will be easier if I tell it just as he told it to me:

(Andy speaking)

I felt more relaxed after smoking up with Pete. The pot had thrown a curtain over the things I’d been feeling since the divorce. Darlene had never been a big socializer. We had hardly ever spent time with friends together, though she spent a lot of time with her girlfriends without me.

I looked around, checking out the women. There were some really good looking ones. Most of them had their summer shorts or sundresses on, showing plenty of legs and bare shoulders.

As an ‘outsider’, too, I couldn’t really make any overtures, even if I felt up to it. I didn’t know which of them was a wife or girlfriend and which was not, except the girls who were clearly too young for that. I spotted an empty chair and collapsed into it. Closing my eyes, I just listened to the music and the laughter around me.

A few minutes later a feminine voice brought me out of my reverie. “Are we boring you?” it said.

Opening my eyes, I saw a pretty brunette, maybe in her mid-twenties, with a nice smile (and perky little tits). “Oh. Nope. I was just enjoying the ‘ambience’.” She sat in the chair next to me. She introduced herself as Melanie. “Are you a resident, friend or relative here?” I asked her.

“Oh, I’m a tourist. My uncle and aunt live here. Maybe you know the Sanders’ family?”

“Um, I don’t know. I’m a ‘tourist’ too. My buddy Pete invited me.” I indicated Pete, standing at his grill.

“Oh, I haven’t met him yet.” At my suggestion, we walked the short distance and I introduced them. Pete smiled and shook hands. He knew her family, but admitted he didn’t know them well. Then he suggested we grab a burger and some potato salad, so we did.

Our chairs had been taken by others, so we walked a bit away, to a picnic table somebody had carried out into the sun. It was quieter there and we got to know each other a little bit as we ate.

Melanie wore a yellow sundress that stopped an inch or so above her knees. It left her shoulders and upper chest bare, with a tiny bit of cleavage. A very decent dress, I thought. Our plates emptied and we stayed at the table.

“You know you’re a very attractive woman,” I told her. “But you hear that all the time, I guess.”

“Why, thank you, sir! But actually, I haven’t heard it too much. It’s always nice to hear.” Her smile put cute little dimples on her cheeks and a sparkle in her green eyes. I felt my interest rise as we talked. She was intelligent and educated (she has a degree in business management, she said). Discarding our plates, we wandered around. She introduced me to her relatives. Her uncle seemed decidedly unfriendly, though I’d noticed he had been having a pretty good time earlier.

Moving away, we went to see what was going on around one of the pools. The owner, who had volunteered for lifeguard duty, was one of Pete’s friends I had met before, and we talked to him a while. A few kids splashed in the pool.

Since neither of us was dressed for swimming, we continued our ramble back toward the front, going through a narrow side yard. I stopped her and turned toward her. “I know this is crazy, but would you mind if I kissed you?” I know my cheeks were red. I’d never really asked a girl like that before. I have always just responded to her signals.

But Melanie smiled and snaked her arms around my waist. “I think that would be a fine thing to do,” she said.

I put my arms around her warm shoulders and we kissed. We kissed again. Then we kissed, letting our tongues get acquainted a little. I felt her smallish but solid breasts pressing against my chest. I was getting hot and it seemed she was too. When she pulled back I was surprised to see that her sunny expression had clouded over.

“Uh-oh. So it wasn’t such a nice thing?” I was puzzled. Then her eyes started to tear up.

“No, no, it WAS a very nice kiss. It’s just that ... I guess I should have told you before it got this far.” She wasn’t touching me at all then. I just waited. She sniffled and swiped at the few tears. “I’m not exactly the person you think, Andy. I’m ... different.”

“Yes, you are different,” I said. “You’re several cuts above any woman I know, or have known,” I added honestly.

“Well, thanks for that, too, but ... well.” She moved back another step. “But I have to tell you something.” She turned away and, taking a deep breath, she said, “I was born male, Andy.” Her voice had been barely above a whisper.

To say I was stunned would be putting it mildly. I’d seen trans people before, but usually it was easy to tell there was something ‘different’ about them, especially if they were male to female transgendered.

Without turning back to me ‘she’ just started to walk away. “Hey Melanie!” I stopped her. With a hand on her arm I turned her back to face me. She was crying in earnest now. I used my handkerchief to wipe her tears as she frowned. “Hang on, a second, will you?” I begged her. “You can’t just run away. That’s a pretty big announcement, you know. Anybody would be surprised. Don’t hold that against me.

“Can we go back to the table and talk about this?” I asked.

“Why? So you can criticize me? So you can treat me like a freak? No thanks, buster!”

“NO!” My voice was too loud, but I didn’t want to just cut things off at that point. In a softer voice, I said. “I just want to talk with you a while. I’m having a great time with you. I just need to wrap my head around this.” She turned to me again with a doubtful look on her face. She nodded.

Back out front, we got new drinks and sat. Before, she had seated herself next to me. Now she was across the table. “First of all,” I began, “I still want to be friends, no matter what, okay?” She looked up at me with doubt in her eyes. “Honestly,” I added. I reached across and put my hand over hers. She glanced down and then back at me, frowning. “If the kiss was so nice for you, well it was great for me. I hope I can kiss you again,” I admitted.

“Are you one of those guys who just...”

“Stop. I’m being sincere, Melanie. You’re the first woman I’ve kissed since my divorce.”

“But I told you...”

“Yeah, you told me. It doesn’t change the fact that I like you. I liked you enough to kiss you.”

“You thought I was a woman then, Andy,” she said.

“As far as I’m concerned, you are a woman. There’s nothing masculine about you.”

She gave a short, bitter laugh. “You wouldn’t say that if you saw me naked,” she said. It dawned on me then. She still hadn’t gone through the final surgery. That made me think. But I shrugged.

“We can still be friends, can’t we? Don’t you have friends?”

With a sigh she said, “Not many. A lot fewer since I came out as trans.”

“I’m sure that’s true, unfortunately.”

“So, me being ... me ... it doesn’t bother you?”

I shook my head. “Nope. I liked you before and I like you even more since you told me. I admire your strength and honesty.” I took her hand again.

She studied my eyes for a long time. Then she said, “Hmm. Okay, we’ll try this, but...”

“‘But’ nothing,” I said firmly. “We can be friends and see how that feels. May I ask you some questions ... friend?”


“When did you realize you weren’t meant to be a guy?”

“At least you didn’t say ‘decide to be a girl’,” she laughed. “That’s the way most people see it. They think it is a decision, but it’s not.”

“I’m aware of that. It is no more a decision than ‘deciding’ to be hetero- or homosexual. I read a lot, Mel.”

“Please, Andy, don’t call me ‘Mel’. It makes me feel funny.”

“Okay. Sorry. I knew another Melanie once and she liked the nickname.” She nodded.

“To answer your question, I guess it was always there, but I didn’t realize why my parents kept buying me boy’s toys when I preferred dolls. I was in sixth grade when I finally discovered the wonderful world of sexuality.

“I went to the library and found some books. At first, I thought I was gay. But it wasn’t that I was more attracted to other boys, not just that, I mean.”

Melanie told me about finding out that she liked the silken feel of putting on her mother’s slips and panties. “So many times I wished I’d been born a female. Like I said, I was only in sixth grade, but, as you probably know yourself, erections begin long before that, even if there doesn’t seem to be a reason for them.”

She shyly admitted that it was one day when she was alone and doing her new favorite thing of trying on her mom’s undies, that she’d had her first orgasm. She laughed again as she told me, “I hid those things deep in the laundry hamper. My parents never liked it when I did ‘girly things’, like spending a long time in the bathroom or using moisturizing lotion after a shower. Having them learn I liked cross-dressing would not have been good, to say the least.”

I stopped her. “Do you want to go for a ride? It’s a little crowded here to be having this talk.” People kept walking past us, causing us to break off what we were saying. She looked around us and back at me, then nodded.

“Is it a good idea for us to leave together? I mean, my aunt and uncle know about me. They accept it and allow me to visit them – even though my parents don’t. Uncle George is uncomfortable with it, but Aunt Judy is okay.” I considered a second.

“Let me go tell Pete we’re going to the liquor store or something. There’s no tequila here, and you just discovered a thirst for it. You don’t live here, so I volunteered to take you to the store. How’s that?”

“I hardly ever drink, though. But okay. Let me get my purse.” She rose and went toward a house. I went over to where Pete was cleaning up his grill.

“Hey, man, Nice party. Thanks for inviting me.”

“Not a problem. You know you’re always welcome. Seems like you and George’s niece have hit it off. She’s a looker, isn’t she?”

I nodded and glanced around. Then I whispered, “Did you know she’s transgendered?” Pete nearly dropped his brush and his eyes went wide for a second.

In a near whisper, he replied, “Jesus! I would never have guessed. So ... What ... I mean, why are you interested?”

I shrugged. “Don’t say anything to anybody, okay? She’s a nice person. I don’t care whether she was born male or not. I have to say, she’s the first friend I’ve made since the divorce. Notice I said ‘friend’. Nothing more than that. She’s in bad shape emotionally.

“Anyway, she wants a shot of tequila. You guys don’t have any, so I’m going to give her a ride to the store.” Melanie joined us as I finished saying that.

Pete glanced her way and said, “Sure, go ahead. Are you coming back?”

I assured him we would be back soon. He asked me to pick up some more vanilla ice cream, since they were running short. I turned down his offer to pay for it.

When we passed the lake, I pulled off and stopped. I asked Melanie if I could kiss her again. Both eyes and her mouth opened wide. “You know I have a dick, but you want to kiss me again. Are you gay?”

I assured her I was not. “Bisexual, then?”

“I don’t know. We both need physical contact and a friend, though, okay?”

We kissed again. That time it lasted a long time. She took my hand and wrapped it around her right breast. I sighed into her mouth and we broke the kiss briefly. “Thank you, Melanie.” I gave her tit a gentle squeeze and went back to kissing her.

When her hand found my growing cock, I pressed against it with gratitude. That time, she backed off and whispered, “Would you like me to suck you?” I put her hand on my zipper.

She bared my fully erect prick and smiled. “Has anybody with a penis ever sucked you off before?”

“No,” I said. “Nor have I ever sucked a penis ... yet.” Her surprise showed again, briefly before she smiled again and bent to her ‘task’. She was good. I rarely orgasm from oral sex, but that day it didn’t take long. There wasn’t a drop visible when she was finished, though, even though my orgasm was stronger than usual.

She sat back but I pulled her to me again. Like most guys, if not all, I’ve tasted my own semen before. It didn’t bother the deep kiss I gave her then. She made a soft sighing sound and I felt a rigidity go out of her shoulders.

She rested her head on my chest for a few minutes. She took the hand not occupied with hugging her and slid it under her dress to her crotch. Her dick was as hard as mine had been. She was built small, though not tiny. It was slender and it felt about an inch shorter than me. I squeezed her and slipped under her panties to stroke it briefly.

But I kissed her and said, “If we’re going back we should go to the store. We don’t have to go back,” I told her. But she shook her head.

“Yes, we do. Pete asked for ice cream. Let’s hurry and get the stuff.”

Back on the road, she told me, “Andy, you’re the third man I’ve kissed since my tits grew (they’re real, not plastic) and the first who didn’t run away when I told him what I was.”

“You mean ‘who’ you are, not ‘what’. You are a person, not an object, Melanie.”

“Are you for real? I mean this is kind of sudden, Andy. Or are you used to kissing trannies?”

“I have never even met one, that I know of, let alone kissed them.”

We made the run and returned. She and I each had a shot of tequila, but that was all I had. Melanie asked for another and I carried two more shots back and set them both in front of her.

“One of these is for you, isn’t it?” she asked.

I told her I didn’t want to drink more because I was driving. She gave me her address and phone number before I thanked Pete again. I had a lot of thinking to do. He stopped me just as I turned to go. “Here, this seemed to help you earlier.” He stuck two joints in my shirt pocket. I thanked him.

As I drove, I dug deep into myself. I imagined Melanie nude. It wasn’t difficult, thanks to the internet. I’d seen pictures, but not pictures of HER naked. The sight of a beautiful woman with breasts and a hard on intrigued me.

My ex-wife was staunchly prejudiced against the whole group of people called, now ‘LGBTQ’. I’m more of a ‘live and let live’ kind of guy, though. I knew guys in the past who were – either secretly or openly – gay or bi, though the idea of going to bed with another guy had never attracted me. I was curious about it all, I admit.

Darlene and I had occasionally included ass play in our sex, but she had denied me the possibility of actually fucking her ass. I briefly wondered as I drove, but decided it wasn’t the reason I had not pushed Melanie away after she told me about herself. So she has a dick. Well, for the time being, we were friends with ‘some’ benefits. At least it was a beneficial blow job she’d given me.

I love licking a woman’s pussy. I don’t care if we just fucked and I’d filled her up. The combination of my cum and hers makes a delicious snack. Could I suck a cock with the same enjoyment? Before Melanie, I wouldn’t have thought so. Now I wasn’t sure. Besides, my inner voice said, I ‘owed her one’. A shiver went down my back at the thought.

She lived in a small city about an hour away from our town. I had planned to wait at least two weeks before calling her, but found myself listening to her phone ring on the other end just a few days later. “Hello?”

“Hi, Melanie. It’s Andy.”

“Yeah, so the phone told me. What’s Up?”

“I just wanted to make sure you were okay. Are you busy?”

“Not at all.”

“I just wanted to talk a while. I felt I should tell you about what I’d been thinking, is all. Unless you’d rather we talk face to face, though.”

“No, actually, this makes it easier for me, I think.”

So I told her everything I’d been thinking. I told her everything. I admitted that I was curious, but that I was sincere when I told her I like her. “I’m not just out to satisfy my curiosity, Melanie. I hope you know that.”

“You know that I wondered at first,” she said. “But I trust what you told me the other day. I trust you even more now, after what you’ve said tonight. But you don’t have to return the favor, Andy. We can just be friends if that’s what you want. I might want to suck you off once in a while if that’s okay.”

I laughed. “Oh, I guess that would be ‘okay’! Shit, you almost sucked me dry. That was a better blow job than any other woman ever gave me.” She giggled.

“I’ve only done that three times before. If it’s good, then I guess I’m a natural. And, even though I told you that you don’t owe me, I’m available if you want to see about your other curiosities. I promise I’m healthy, I have the proof in writing.”

“I’m also healthy, though I haven’t been tested.”

“Would you be insulted if I asked you to get tested? It’s free at the health clinic.”

“Not at all. You never know. Maybe some of Darlene’s ‘girls’ nights’ were something different.” It couldn’t hurt, I thought. I had even considered it after we split up, but I never did. “How about if I drive into town Friday? We can go together to the clinic. You can hold my hand.”

With a laugh, Melanie said she’d be happy to do it. “Afterward, maybe I can hold more than your hand.”

“Ah. I was going to suggest that we could spend the weekend together.”

“Wow! Cool! What time Friday?”

“Not too early,” I said. “What time does the clinic open?”

I got to town about 9:30. Melanie and I had decided to meet at a coffee shop down the block from the clinic. She was waiting when I got there. Her smile was a beautiful thing. I ordered a coffee and joined her at her table. I bent to give her a brief kiss before I sat down. “You smell great,” I told her.

“You too,” She said. We chatted some over our coffee before going to the clinic. After they drew my blood we strolled around a little bit. We approached a drug store and Melanie shyly asked if I needed to go in for anything. I gave her a proper kiss then. People strolled past but nobody knew us so I didn’t care. All they saw was a man kissing a woman.

I whispered to her that I had been a Boy Scout. In other words, I was prepared. She squeezed me and I could feel her nipples and prick against me. I began to stiffen so I broke off before it became obvious to everybody. “After last week, I sure hope your test comes back negative. I should not have done that without knowing if it was safe.”

“No. You’re right.”

“I can’t explain how you make me feel though. By the time we were in your car I just couldn’t help myself.”

“I’ve never felt this way either. I don’t care if I’ll have occasion to use any condoms this weekend or not. I just enjoy being with you. It’s what’s inside that matters to me, Melanie.”

She let me hold her and we snuggled a few more seconds before continuing our walk. I steered us to my car and we drove off. I asked her where we should go and she gave me directions. She pointed to a parking spot and we got out. I saw we were in a residential area and looked at her. She grinned and took my hand. She led me up the walk to a small house like many of its neighbors.

Finding her key, she led me inside. What do you think?” she asked me.

I looked around. It was nice and felt like a home, not a house. I could tell Melanie had made it that way. “It’s nice,” I said. “It feels like a home, not just a place to stay for a while.”

“Thanks. I’m no interior decorator, though. I’m sure everything doesn’t exactly match, but...” she shrugged, hands raised to the side.

“It’s great,” I said. “But I’ve been told I have no aesthetic taste.” We laughed and she led me to the kitchen.

She offered me some iced tea, which I accepted. “Since my divorce I’ve usually used beer for breakfast and whiskey for dinner. This week I hardly had a drink. Even Pete mentioned I looked better at work.”

“Yeah, booze can really take it out of you. You don’t notice at first but it gets worse. I had some friends who dove too deep. One of them died from it. Maybe more did too, I don’t keep in touch.”

“I never went to any of my class reunions. I was only in that high school a year before graduating, and I was never close with anybody in college. That’s just the past,” I said.

“Yeah, I agree. Funny story, though: I ran into one of the guys I went to high school with one day. He didn’t recognize me, though. He hadn’t seen me since my hair grew and I got tits. He leered at me but I just went on my way.”

She looked up at me suddenly. “Hey, do you mind helping me out back? I have a pile of lumber to move and some of it is too heavy for one pair of hands.”

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Story tagged with:
Ma/Ma / Consensual / Romantic / BiSexual / Shemale / Fiction / Anal Sex / First /